2550-40-5

Basic information

• Product Name: Cyclohexyl disulfide
• Synonyms: CYCLOHEXYL DISULFIDE;CYCLOHEXYLDISULPHIDE;DICYCLOHEXYL DISULFIDE;DICYCLOHEXYL DISULPHIDE;FEMA 3448;bis(cyclohexyl)disulfide;Disulfide,dicyclohexyl;DICYCLOHEXYL DISULFIDE 94+%
• CAS NO: 2550-40-5
• Molecular Formula: C₁₂H₂₂S₂
• Molecular Weight: 230.43
• EINECS: 219-851-6
• Product Categories: sulfide Flavor
• Mol File: 2550-40-5.mol
• Article Data: 162

Chemical Properties

• Melting Point: 127-130 °C
• Boiling Point: 162-163 °C6 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: COA
• Density: 1.046 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.000305mmHg at 25°C
• Refractive Index: n20/D 1.545(lit.)
• Storage Temp.: Inert atmosphere,Room Temperature
• Water Solubility: Immiscible with water.
• BRN: 1905920
• CAS DataBase Reference: Cyclohexyl disulfide(CAS DataBase Reference)
• NIST Chemistry Reference: Cyclohexyl disulfide(2550-40-5)
• EPA Substance Registry System: Cyclohexyl disulfide(2550-40-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• RIDADR: 3334
• WGK Germany: 3
• RTECS: JO1843850
• TSCA: Yes
• Hazardous Substances Data: 2550-40-5(Hazardous Substances Data)

Usage

Chemical Properties

Dicyclohexyl disulfide has a berry, musty, green, alliaceous odor

Uses

Dicyclohexyl disulfide is employed as an edible spices. It is also used in dyes, medicine and organic synthesis. It is also useful as a synthetic flavor ingredient. Further, it is used in the production of n-(cyclohexylthio) phthalimide.

Taste threshold values

Taste characteristics at 5 ppm: onion, meaty, clam, crab, coffee and cocoa.

InChI:InChI=1/C12H22S2/c1-3-7-11(8-4-1)13-14-12-9-5-2-6-10-12/h11-12H,1-10H2

Synthetic route

Cyclohexanethiol (1569-69-3) → 1,2-dicyclohexyl disulfide (2550-40-5)

Conditions	Yield
With 2,2'-bipyridylchromium peroxide In benzene for 0.7h; Product distribution; Heating; effect of various chromium(VI) based oxidants;	100%
With 2,2'-bipyridylchromium peroxide In benzene for 0.7h; Heating;	100%
With tris paraperiodate In benzene for 1h; Heating;	100%

Cyclohexanethiol (1569-69-3) → 1,2-dicyclohexyl disulfide (2550-40-5) + C12H22S2Se

Conditions	Yield
With bis-(benzotriazol-1-yl)selenide In dichloromethane for 3h;	A n/a B 92%

1-bromocyclohexane (108-85-0) → 1,2-dicyclohexyl disulfide (2550-40-5)

Conditions	Yield
With sodium sulfide trihydrate; hexachloroethane at 20℃; for 2.5h; Reagent/catalyst;	90%
With dimethyl sulfoxide; thiourea; 1,1,1,3,3,3-hexamethyl-disilazane In water at 50℃; for 24h;	89%
With Sodium thiosulfate pentahydrate; water; dimethyl sulfoxide at 60 - 70℃; for 12h; pH=< 3;	89%

diphenylmethyl cyclohexyl thioether → 1,2-dicyclohexyl disulfide (2550-40-5)

Conditions	Yield
With iodine In dichloromethane for 2h; Heating;	89%

1-iodocyclohexane (626-62-0) → 1,2-dicyclohexyl disulfide (2550-40-5)

Conditions	Yield
With indium(III) oxide; ammonia; water; sulfur In ethanol at 60℃; Green chemistry;	89%

1-bromocyclohexane (108-85-0) + thiourea (17356-08-0) → 1,2-dicyclohexyl disulfide (2550-40-5)

Conditions	Yield
With tetrachloromethane; water; triethylamine In glycerol at 50℃; for 24h;	87%
With sodium carbonate In water; acetonitrile at 80℃; for 12h;	70%

1-bromocyclohexane (108-85-0) + Cyclohexanethiol (1569-69-3) → 1,2-dicyclohexyl disulfide (2550-40-5)

Conditions	Yield
With sodium thiosulfate	85%

sodium cyclohexylthiosulfate → 1,2-dicyclohexyl disulfide (2550-40-5)

Conditions	Yield
With choline chloride; dihydrogen peroxide; toluene-4-sulfonic acid In water at 60℃; for 6h;	83%
With 1H-imidazole; water at 70℃; for 0.583333h; Green chemistry;	75%

cyclohexanol (108-93-0) → 1,2-dicyclohexyl disulfide (2550-40-5)

Conditions	Yield
Stage #1: cyclohexanol With 1,2-bis(5-methylisoxazol-3-yl)hydrazine; triphenylphosphine In acetonitrile at 80℃; for 0.333333h; Mitsunobu Displacement; Stage #2: With ammonium thiocyanate In acetonitrile at 80℃; for 6h; Reagent/catalyst; Mitsunobu Displacement;	81%

para-xylene (106-42-3) + 1-oxa-4-thiaspiro-<4,5>decan-2-one (1564-39-2) → 1,2-dicyclohexyl disulfide (2550-40-5) + 2-cyclohexylthioacetic acid (52363-15-2) + 5',8'-dimethylspiro-4'-one (141622-51-7) + <<1-(2',5'-dimethylphenyl)cyclohexyl>thio>acetic acid (141622-65-3)

Conditions	Yield
With aluminium trichloride for 24h; Ambient temperature; Further byproducts given;	A 3% B 4% C 80% D 5%

cyclohexyl(4-methoxybenzyl)sulfane (93394-70-8) → 1,2-dicyclohexyl disulfide (2550-40-5) + 4-methoxy-benzaldehyde (123-11-5) + p-methoxybenzyl chloride (824-94-2)

Conditions	Yield
With 2,6-dimethylpyridine; tris-(4-bromophenyl)aminium hexachloroantimonate In dichloromethane; acetonitrile for 1h; Mechanism;	A 80% B n/a C 80%

S-nitrosocyclohexanethiol (15459-94-6) → 1,2-dicyclohexyl disulfide (2550-40-5)

Conditions	Yield
With air In chloroform at 20℃; for 0.416667h;	80%
In dichloromethane at 20℃; for 1.83333h; Elimination; dimerization;

tricyclohexyltin(IV) chloride (3091-32-5) → 1,2-dicyclohexyl disulfide (2550-40-5)

Conditions	Yield
With sulfur; cesium fluoride In N,N-dimethyl-formamide at 130℃; for 48h; Substitution;	80%
With sulfur; potassium fluoride In water; N,N-dimethyl-formamide at 150℃; for 22h;	50%

ferrocene (102-54-5) + 1-oxa-4-thiaspiro-<4,5>decan-2-one (1564-39-2) → Cyclohexanethiol (1569-69-3) + η5-cyclopentadienyl(4',7'-dihydro-4'-oxo-η-4'a-7'a-spiro{cyclohexane-1,1'(3'H)-cyclopenta{c}thiopyran}yl)iron + 1,1'-{cyclohexylidenethio(2-oxoethylene)}ferrocene + 1,2-dicyclohexyl disulfide (2550-40-5)

Conditions	Yield
aluminium trichloride In carbon disulfide excess ferrocene, mixture is stirred for 24 h at room temp.; addn. of 10% HCl soln., extn. with CHCl3 and CH2Cl2, ext. is washed with water, aq. Na2CO3 soln., water; dried over MgSO4, solvent is removed by distn. under reduced pressure, HPLC, preparative thin layer chromy.;	A 2% B 5% C 80% D 2%

Cyclohexanethiol (1569-69-3) + di-n-propyl phosphonate (1809-21-8) → 1,2-dicyclohexyl disulfide (2550-40-5) + S-cyclohexyl O,O-dipropyl thiophosphate

Conditions	Yield
With 1,3-dichloro-5,5-dimethylhydantoin In dichloromethane at 20℃; for 0.166667h;	A n/a B 80%

Cyclohexanethiol (1569-69-3) + 2-mercaptothiazole (5685-05-2) → 2,2'-di(thiazol-2-yl)disulfide (20362-54-3) + 1,2-dicyclohexyl disulfide (2550-40-5) + C9H13NS3

Conditions	Yield
With 4,6-di-tert-butyl-N-(tert-butyl)-o-aminophenol In acetonitrile at 20℃; for 4h; Electrochemical reaction;	A n/a B n/a C 72%

1-cyclohexyltho-2-triethylsilylethyne (1015423-93-4) → 1,4-Bis(triethylsilyl)buta-1,3-diyne (17047-96-0) + 1,2-dicyclohexyl disulfide (2550-40-5)

Conditions	Yield
With P(p-CH3OC6H4)3; rhodium hydrido (PEt3)3 complex In acetone for 2h; Heating;	A 71% B n/a

1-oxa-4-thiaspiro-<4,5>decan-2-one (1564-39-2) + benzene (71-43-2) → Cyclohexanethiol (1569-69-3) + 1,2-dicyclohexyl disulfide (2550-40-5) + cyclohexyl phenyl sulphide (7570-92-5) + 2-cyclohexylthioacetic acid (52363-15-2) + spiro-4'-one (141622-49-3) + <<1-(phenyl)-cyclohexyl>thio>acetic acid (141622-63-1)

Conditions	Yield
With aluminium trichloride for 24h; Product distribution; Mechanism; Ambient temperature; other arenes;	A 2% B 3% C 2% D 5% E 70% F 6%

sodium cyclohexanethiolate (50729-68-5) + benzenediazonium o-benzenedisulfonimide → 1,2-dicyclohexyl disulfide (2550-40-5) + cyclohexyl phenyl sulphide (7570-92-5) + sodium o-benzenedisulfonimide

Conditions	Yield
In methanol at 0 - 5℃; Dimerization; alkylthiodediazoniation;	A 11% B 67% C n/a

Cyclohexanethiol (1569-69-3) + allyl bromide (106-95-6) → 1,2-dicyclohexyl disulfide (2550-40-5) + (3-(cyclohexylthio)propylthio)cyclohexane (115412-67-4)

Conditions	Yield
With water; silica gel for 18h; Mechanism; regioselective reaction;	A n/a B 67%

cyclohexyl tosylate (953-91-3) → 1,2-dicyclohexyl disulfide (2550-40-5)

Conditions	Yield
With silica gel at 20℃; for 0.25h;	65%

Cyclohexanethiol (1569-69-3) + allyl bromide (106-95-6) → 1,2-dicyclohexyl disulfide (2550-40-5) + (1-(cyclohexylthio)propan-2-ylthio)cyclohexane

Conditions	Yield
With silica gel for 10h; Mechanism; regioselective reaction;	A n/a B 65%

cyclohexane (110-82-7) → 1,2-dicyclohexyl disulfide (2550-40-5)

Conditions	Yield
With sulfur; di-tert-butyl peroxide at 120℃; for 24h;	61%
With sulfur dichloride Irradiation;

Cyclohexanethiol (1569-69-3) + para-chlorotoluene (106-43-4) → 1,2-dicyclohexyl disulfide (2550-40-5) + (4-methylphenyl)cyclohexyl sulfane (59693-93-5)

Conditions	Yield
With caesium carbonate In dimethyl sulfoxide at 110℃; for 24h; Inert atmosphere; chemoselective reaction;	A n/a B 55%

Cyclohexanethiol (1569-69-3) + 4-bromobenzenecarbonitrile (623-00-7) → 1,2-dicyclohexyl disulfide (2550-40-5) + 4-cyanophenyl cyclohexyl sulfide (288588-24-9)

Conditions	Yield
With tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; (1,2-dimethoxyethane)dichloronickel(II); triethylammonium bis(1,2-benzenediolato)phenylsilicate; 4,4'-di-tert-butyl-2,2'-bipyridine In N,N-dimethyl-formamide at 27℃; for 36h; Inert atmosphere; Irradiation;	A 6% B 46%

Cyclohexanethiol (1569-69-3) + 2-propanethiol (75-33-2) → diisopropyl sulfide (4253-89-8) + 1,2-dicyclohexyl disulfide (2550-40-5) + 1-cyclohexyl-2-isopropyldisulfane

Conditions	Yield
With 4,6-di-tert-butyl-N-(tert-butyl)-o-aminophenol In acetonitrile at 20℃; for 4h; Electrochemical reaction;	A n/a B 46% C 40%

Cyclohexanethiol (1569-69-3) + thiophenol (108-98-5) → 1,2-dicyclohexyl disulfide (2550-40-5) + 1-cyclohexyl-2-phenyldisulfane (29627-27-8) + diphenyldisulfane (882-33-7)

Conditions	Yield
With 4,6-di-tert-butyl-N-(tert-butyl)-o-aminophenol In acetonitrile at 20℃; for 4h; Electrochemical reaction;	A n/a B 15% C 41%

C22H31FeN6S(1+)*C24H20B(1-) → 1,2-dicyclohexyl disulfide (2550-40-5) + S-cyclohexyl cyclohexane-1-sulfonothioate (4837-39-2)

Conditions	Yield
With oxygen In dichloromethane at 20℃; for 1h;	A 35% B 14%

cyclohexylmagnesium bromide (931-50-0) → 1,2-dicyclohexyl disulfide (2550-40-5) + ammonium S-cyclohexyl thiosulphate (76160-80-0)

Conditions	Yield
With tetrasulphure tetranitride In benzene Ambient temperature;	A 30% B 19%

disulfane (23550-45-0) + cyclohexene (110-83-8) → 1,2-dicyclohexyl disulfide (2550-40-5) + dicyclohexyl sulfide (7133-46-2) + hydrogen sulfide (7783-06-4)

Conditions	Yield
50°C; 15 h;	A 7.42% B 7.75% C 29.6%

1,2-dicyclohexyl disulfide (2550-40-5) + sodium 4-methylbenzenesulfonothioate (3753-27-3) → S-cyclohexyl 4-methylbenzenesulfonothioate (37556-51-7)

Conditions	Yield
With iodine In dichloromethane	99%

1,2-dicyclohexyl disulfide (2550-40-5) → cyclohexanesulfonyl chloride (4837-38-1)

Conditions	Yield
With dihydrogen peroxide; zirconium(IV) chloride In water; acetonitrile at 25℃; for 0.0166667h;	98%
With N,N,N',N'-tetrachlorobenzene-1,3-disulphonamide; tetrabutyl-ammonium chloride; water In acetonitrile at 0 - 20℃; for 0.333333h;	98%
With trichloroisocyanuric acid; tetrabutylammomium bromide; water In acetonitrile at 0 - 20℃; for 0.333333h;	98%

1,2-dicyclohexyl disulfide (2550-40-5) + C20H15NOS (1316303-52-2) → 3-(cyclohexylthio)-2,4-diphenyl-2,1-benzothiazine 2-oxide (1450818-82-2)

Conditions	Yield
Stage #1: C20H15NOS With n-butyllithium In tetrahydrofuran at -78℃; for 0.166667h; Inert atmosphere; Stage #2: 1,2-dicyclohexyl disulfide In tetrahydrofuran Inert atmosphere;	98%

1,2-dicyclohexyl disulfide (2550-40-5) + (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl phenylphosphinate (31352-60-0, 31352-61-1, 54353-18-3) → (Rp)-S-cyclohexyl O-menthyl phenylphosphonothioate

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) In neat (no solvent) at 80℃; for 16h;	98%

1,2-dicyclohexyl disulfide (2550-40-5) + N,N-dimethyl-2-(2-phenylethynyl)aniline (54655-08-2) → 3-(cyclohexylthio)-1-methyl-2-phenyl-1H-indole (1346164-94-0)

Conditions	Yield
With iodine; iron In acetonitrile at 80℃; for 3h; Inert atmosphere;	97%

1,2-dicyclohexyl disulfide (2550-40-5) → S-cyclohexyl cyclohexane-1-sulfonothioate (4837-39-2)

Conditions	Yield
With 1H-imidazole; manganese(II) tetraphenylporphyrinate; tetra-n-butylammonium hydrogen monopersulfate In dichloromethane at 20℃; for 0.0166667h;	96%
With N2O4*polyvinylpyrrolidone In chloroform at 20℃; for 3h;	92%
With Oxone; potassium bromide In water; acetonitrile at 20℃; for 0.366667h;	90%

1,2-dicyclohexyl disulfide (2550-40-5) + hexamethyldistannane (661-69-8) → [CySSnMe3] (264926-03-6)

Conditions	Yield
In benzene Irradiation (UV/VIS); stirred at 35°C for 7 h;	95%
In benzene Irradiation (UV/VIS); stirred at 35°C for 4 h;	60%

1,2-dicyclohexyl disulfide (2550-40-5) + 4-methoxy-phenol (150-76-5) → C13H18O4S (59416-28-3)

Conditions	Yield
Stage #1: 1,2-dicyclohexyl disulfide With tetrabutyl-ammonium chloride; water; chloroamine-T In acetonitrile at 0℃; for 0.5h; Stage #2: 4-methoxy-phenol With triethylamine In acetonitrile at 0 - 20℃; for 1h;	95%

1,2-dicyclohexyl disulfide (2550-40-5) → cyclohexanesulfonyl bromide (42738-18-1)

Conditions	Yield
With N-Bromosuccinimide In water; acetonitrile at 20℃; for 3h;	94%
With sodium hypochlorite pentahydrate; acetic acid; sodium bromide for 0.25h;	92%

1,2-dicyclohexyl disulfide (2550-40-5) + sodium p-chlorobenzenesulphinate (14752-66-0) → S-cyclohexyl p-chlorobenzenethiosulfonate (361477-24-9)

Conditions	Yield
With iodine In dichloromethane at 20℃; for 2h;	93%

1,2-dicyclohexyl disulfide (2550-40-5) + 5-nitro-N-(2-(pyridin-2-yl)propan-2-yl)thiophene-2-carboxamide → 3-(cyclohexylthio)-5-nitro-N-(2-(pyridin-2-yl)propan-2-yl)thiophene-2-carboxamide

Conditions	Yield
With copper diacetate; sodium carbonate In 1,4-dioxane at 130℃; for 12h;	93%

carbon monoxide (201230-82-2) + 1,2-dicyclohexyl disulfide (2550-40-5) + diethylamine (109-89-7) → S-cyclohexyl-N,N-diethylcarbamate

Conditions	Yield
tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran at 120℃; under 38000 Torr; for 48h;	92%

1,2-dicyclohexyl disulfide (2550-40-5) + 4,4'-dimethoxyphenyl disulfide (5335-87-5) → 1-(cyclohexyldisulfanyl)-4-methoxybenzene (735269-14-4)

Conditions	Yield
With potassium tert-butylate In tetrahydrofuran at 60℃; for 8h;	91%

1,2-dicyclohexyl disulfide (2550-40-5) → Cyclohexanethiol (1569-69-3)

Conditions	Yield
With tetrabutylammonium borohydride In tert-butyl alcohol for 5h; Heating;	90%
With cobalt-polysulfide at 150 - 185℃; under 47808 Torr; Hydrogenolyse;
With molybdenum-polysulfide at 150 - 185℃; under 47808 Torr; Hydrogenolyse;

1,2-dicyclohexyl disulfide (2550-40-5) + sodium benzenesulfonate (873-55-2) → S-cyclohexyl benzenesulfonothioate

Conditions	Yield
With iodine In dichloromethane for 22h;	90%
With iodine In dichloromethane at 20℃; for 10h;	89%
With N-Bromosuccinimide In acetonitrile at 20℃; for 15h;

1,2-dicyclohexyl disulfide (2550-40-5) + 4-aminotiophenol (1193-02-8) → 4-(cyclohexyldisulfanyl)aniline

Conditions	Yield
With potassium tert-butylate In tetrahydrofuran at 60℃; for 8h;	90%

4-Methoxybenzenethiol (696-63-9) + 1,2-dicyclohexyl disulfide (2550-40-5) → 1-(cyclohexyldisulfanyl)-4-methoxybenzene (735269-14-4)

Conditions	Yield
With potassium tert-butylate In tetrahydrofuran at 60℃; for 8h;	90%

4-Fluorothiophenol (371-42-6) + 1,2-dicyclohexyl disulfide (2550-40-5) → C12H15FS2

Conditions	Yield
With potassium tert-butylate In tetrahydrofuran at 60℃; for 8h;	89%

1,2-dicyclohexyl disulfide (2550-40-5) + bis(4-fluorophenyl)disulfide (405-31-2) → C12H15FS2

Conditions	Yield
With potassium tert-butylate In tetrahydrofuran at 60℃; for 8h;	89%

1,2-dicyclohexyl disulfide (2550-40-5) + p-Chlorothiophenol (106-54-7) → C12H15ClS2

Conditions	Yield
With potassium tert-butylate In tetrahydrofuran at 60℃; for 8h;	88%

N,N-Dimethylpropargylamin (7223-38-3) + 1,2-dicyclohexyl disulfide (2550-40-5) → N-[(2Z)-2,3-bis(cyclohexylsulfanyl)-2-propenyl]-N,N-dimethylamine (1032739-15-3)

Conditions	Yield
Stage #1: 1,2-dicyclohexyl disulfide With bis(acetylacetonate)nickel(II); Dimethyl(phenyl)phosphine at 20℃; Inert atmosphere; Stage #2: N,N-Dimethylpropargylamin at 100℃; for 2h; Inert atmosphere; stereoselective reaction;	87%

1,2-dicyclohexyl disulfide (2550-40-5) + (2,4,6-trimethylbenzoyl)diphenylphosphine oxide (75980-60-8) → C16H22OS + diphenylphosphinothioic acid S-cyclohexyl ester

Conditions	Yield
In dichloromethane at 20℃; for 6h; Inert atmosphere; Sealed tube; Irradiation;	A 43 %Spectr. B 87%

1,2-dicyclohexyl disulfide (2550-40-5) + sodium 4-methylbenzenesulfinate (824-79-3) → S-cyclohexyl 4-methylbenzenesulfonothioate (37556-51-7)

Conditions	Yield
With iodine at 40℃; for 9h;	86%
With iodine In dichloromethane at 25℃; Inert atmosphere;

indole (120-72-9) + 1,2-dicyclohexyl disulfide (2550-40-5) → 3-(cyclohexylthio)-1H-indole (1210054-37-7)

Conditions	Yield
With iodine In ethanol at 20℃; for 12h;	86%
With iron(III) trifluoride; iodine In acetonitrile at 80℃; for 36h; regioselective reaction;	81%

Upstream product

• 623-11-0 1-methyl-4-nitrosobenzene 
• 856809-29-5 3-cyclohexanesulfinyl-propionic acid 
• 110-83-8 cyclohexene 
• 177-58-2 2,2,4,4,6,6-tris(pentamethylene)-1,3,5-trithiane 
• 108-85-0 1-bromocyclohexane 
• 110-82-7 cyclohexane 
• 106-42-3 para-xylene 
• 1564-39-2 1-oxa-4-thiaspiro-<4,5>decan-2-one 
• 71-43-2 benzene 
• 1569-69-3 Cyclohexanethiol 
• 108-91-8 cyclohexylamine 
• 109-89-7 diethylamine 
• 7647-01-0 hydrogenchloride 
• 23550-45-0 disulfane 

Downstream Products

• 40952-48-5 C₆H₁₁BrS 
• 77636-97-6 N,N'-bis-benzenesulfonyl-cyclohexanesulfinamidine 
• 110-83-8 cyclohexene 
• 361477-24-9 S-cyclohexyl p-chlorobenzenethiosulfonate 
• 37556-51-7 S-cyclohexyl 4-methylbenzenesulfonothioate 
• 916922-05-9 C₁₁H₁₅NO₄S 
• 1210054-37-7 3-(cyclohexylthio)-1H-indole 
• 17797-03-4 cyclohexane sulphenyl chloride 
• 1346164-94-0 3-(cyclohexylthio)-1-methyl-2-phenyl-1H-indole 
• 29627-34-7 4-(phenyldisulfanyl)toluene 
• 95914-29-7 1-(4-methoxyphenyl)-2-phenyldisulfane 
• 83180-92-1 1-(4-methylphenyldisulfanyl)-4-methoxybenzene 

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The efficient and straightforward syntheses of silylthioethers and disulfides are presented. The synthetic methodologies are based on new rhodium complexes containing bulky N-heterocyclic carbene (NHC) ligands that turned out to be efficient catalysts in thiol and thiol-silane coupling reactions. These green protocols, which use easily accessible reagents, allow obtaining compounds containing S-Si and S-S bonds in solvent-free conditions. Additionally, preliminary tests on coupling of mono- and octahydro-substituted spherosilicates with selected thiols have proved to be very promising and showed that these catalytic systems can be used for the synthesis of a novel class of functionalized silsesquioxane derivatives.

Substituted o-Aminophenols as Redox-Mediators in the Thiol Oxidation to Unsymmetrical Disulfides

A number of substituted o-aminophenols has been investigated as redox mediators of the thiol oxidation to disulfides. The electrooxidation of o-aminophenols leads to the corresponding o-iminobenzoquinones. These compounds react with thiols in the solution with a formation of disulfides. It was established that the use of 4,6-di-tert-butyl-2-(tert-butylamino)phenol as a redox mediator can reduce the overpotential of the thiol oxidation by 0.2-1.4 V depending on the nature of the coupling thiols. The unsymmetrical disulfides with alkyl, aryl, and heteroaryl substituents were obtained as the result of the indirect electrosynthesis.